


The Auction

by haze1982



Category: Actor RPF
Genre: Anal Sex, Angst, Blow Jobs, Cigarettes, Gambling, Golf, Hollywood Legends, I Wrote This Instead of Sleeping, M/M, Naked Male Clothed Male, Slave auction, Spanking, booze
Language: English
Status: In-Progress
Published: 2016-12-24
Updated: 2018-07-22
Packaged: 2018-09-11 16:46:27
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 5
Words: 11,816
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8998837
Author URL: https://archiveofourown.org/users/haze1982/pseuds/haze1982
Summary: When Dean is feeling the tension built up between his and Jerry's feud, he decides the best way to deal with it is by distancing himself to the golf course. There, he starts to become closer to Bing who decides to invite him to an Auction.How can he possibly say no to the man he's idolized for so long? Warning: M/M sex, spanking, and all that's in here.





	1. The Auction

The view from the balcony was stunning with the moon hanging high and the stars shining like diamonds. Dean took the cigarette from his silver case, tapping it a few times before he let it rest lazily between his lips and sliding his lighter out of his pocket. He lifted the dancing flame to the cigarette's end and stared at the moon as he deeply inhaled.

Letting out a thin stream of smoke, he had to relax his nerves before it was his turn to take the stage. He had never done anything like this before and he really only got bits of information of what was expected of him tonight. Matter of fact, if anyone aside from Bing had asked him to put himself up for some kind of charity auction, he would have told them to beat it.

He didn't want to date any strange broads.

Dean found himself on the golf course just a few hours before with Bing Crosby and, somewhere around the 13th hole, Bing asked if he'd be interested in the auction that was completely private and the proceeds would go towards a reputable charity.

At first, Dean did try to decline but he was a gambler at heart and decided to give Bing a chance to get his way.

So, they made a deal.

Bing beats Dean at this game of golf, he has to put himself up on that charity auction block.

If Dean beats Bing, he gets to go home and relax for the rest of the evening - alone. Being alone was fine with Dean. He didn't have to worry about being judged by onlookers or have his hair pulled by his partner. Not that he's against hair pulling but the overacting was getting too frequent.

In the end, Dean dropped to his knees and begged Bing not to beat him.

His pleas for mercy were all in vain and he did end up losing the bet. Bing wouldn't even go for a double or nothing Blackjack game.

Dino Paul was no welcher on a gamble and he wouldn't, and couldn't, say no to Bing. The man was, and is,  his idol. What was more important to Dean was they were starting to become pals.

With all the fights and cold shoulders he was getting from Jerry, he could use some pals.

Auctioning himself off was a bit intimidating. You never knew what sort of dame would try to get you. Though, he hoped that a stranger didn't wind up winning him.

The dark man leaned over the railing, letting his elbows rest, and arched his back as he brought a finger up to his lips and took the moment to savor the solitude. He could be in the next room, mingling, but - like most times - he just wasn't feeling the urge to act sociable. All he wanted to do was have a nice, long weekend without being around Jerry and all the hostility.

He jumped a bit when he felt a hand on his right shoulder and a warm, "Out here by yourself, boy?"

Dean turned to look over his shoulder and nodded with a smile.

"Well, apparently not anymore, Bob," Dean replied with a strange sense of calm.

"Gimme a drag off that smoke, goombah."

Dean stood to his full height, laughing off the name. He offered the rest of his cigarette to Bob with a nod, "Sure. G'head and finish it off, paesan."

Bob took the cigarette and inhaled, blowing out the smoke. He watched the smoke fly up to the air and had to ask, "So, really, Charlie. What you doin' out here all by your lonesome?"

"Just waitin' for my turn to get up on that stage tonight for this charity. Wonder what broad's gonna win me..."

"What? You're actually gonna auction yourself? Why?" Bob threw the unfinished cigarette over the balcony and turned to face Dean.

"Sure. Bing told me about it today on the course and how it's for some charity. Wasn't doin' nothin' else tonight. And besides that, I lost a bet with him."

Bob put his hand on the rail and leaned a bit while crossing his right foot over the left one. He squinted his eyes and recalled that Dean said 'broad'. Surely, this kid couldn't be that much in the dark.

"Kid, do you know what's going on here? Really?"

"I just told you all I know, pal. What of it? The money goes to a charity, right?"

Bob bit his lower lip and scratched behind his ear. He slowly looked at Dean and started to get the idea - especially with Bing being the one that invited the Italian to the private party.

"Oh, nothin'. Nothin' at all. I mean, yeah. It goes for a charity. But there aren't any dames biddin', ya know?"

"No dames?"

"Nuh uh. Not a one, meatball."

"Well, who's bidding?"

"Look, kid. First off, don't give yourself an aneurysm.  It's not all bad, so put your tongue back in your mouth. I guess my ol' pal didn't fill you in on everything. So, I will," Bob said and grinned. Normally, he would just stay out of it but he liked Dean. And, damn, was he cute all confused. Bob wasn't a sadist, though, so he elaborated a bit more for the younger man.

 "A few times a year, us older guys in the business will come to this joint in private and bid on the younger guys, you see. It's all for fun and consensual. So, the young guys, you see. They wind up being something of our slaves for the rest of the night. It just helps us unwind is all."

"I'm gonna be somebody's slave? What the -"

"If you want to be someone's slave for the night, I won't stand in your way."

"Hey, now. That was a question - not a statement. I ain't gonna be nobody's slave."

"Not right now. You're going up there soon and I have a feeling I know _exactly_ who has their eye on you, boy. You'd have to be blind not to see it, really."

Dean furrowed his brow and looked at Bob with concern. Bob found Dean's sudden change of demeanor a bit curious as he asked, "You don't mean… Bing?"

Bob just nodded his head and turned around laughing, "Good to see that you're not blind, kid. Dad is such a sneaky, dirty old man."

The realization dawned on Dean and he turned his back to Bob, holding on to the rails with both hands. He couldn't back out now - not from his idol, the man he'd been emulating for as long as he can remember. And aside from that, if he ever lost a bet, he would pay up. Every man on the planet ought to have a code and that was his.

He swallowed and whispered, "Slave."

"Don't worry that pretty little head of yours. The old man is a nice guy and it's only for a night."

"What do you mean by _slave_?"

"Now, I ain't gonna tell all his secrets. You're not completely dumb. I'm sure you can figure it out."

Dean knew if he left now that it wouldn't look good for him but the thought was tempting. Just as he was about to turn around, a young man in a tux came forward.

"Mr. Martin?"

Dean nodded and tried to compose himself from the shock of the news he just heard.

"Mr. Martin, you're needed at the stage. You're on now!"

Still nodding, he smoothed down his jacket and fixed his cuffs to hide his hands. He instinctively rubbed his right pinky before lifting his left hand so he could run his fingers through his jet black hair. He started towards the stage and squinted as the light caught him off guard.

Bob bit his lower lip and followed behind Dean. The older man eyed Dean's form and couldn't blame his partner for inviting the kid.

Dean stood tall and put on his best face as he looked towards the crowd, his eyes searching for Crosby.

He turned his head towards the auctioneer as the older man started, "Good evening, gentleman. Our next boy up for tonight's auction is Dean Martin and this is his first time here. He is half of the Martin & Lewis team and recently had the honor of having his song - _"That's Amore"_ \- reach gold record status. Who knows? Maybe he'll sing it to you in your room if you're the lucky winner! We'll start the bidding, tonight at $500!"

The room sounded with bids:

_$500!_

_$1,000!_

_$1,500!_

_$2,000!_

Dean rubbed his hands together for a moment and could hardly fathom the amounts being bid on him. He recognized Phil Harris' voice shouting out $3,000. The heat from the lighting was causing tiny beads of sweat to fall off the end of his nose and he grabbed his handkerchief, dabbing it off of his forehead. It didn't escape him that there was one voice that hadn't made a sound to bid on him.

The very man gave him the invite.

The thought of someone else winning him in this thing sent flight signals to his brain to get the hell out of there.

When he heard $8,000 being bid on him by Jack Benny, he nearly passed out from shock but kept a smile on his face. Hell was definitely going to freeze over if that man bid (and won) that much on anything.

Apparently, that was too high as the auctioneer started the countdown, "Anyone want to bid $8,500 on Dino! It'll be a night you'll never forget!"

Dean squinted his eyes and saw Bing sitting at his table with his arms crossed. The older man didn't show a hint of emotion nor did he make a peep.

"Going Once!"

Dean arched his neck to the side and looked over at Bob for a moment who shrugged. He stole a quick glance in Jack's direction who started to fidget and looking more than a little worried.

"Going Twice!"

Swallowing again, Dean's eyes darted from Bob to Bing.

"No more bids? Alright, Jack -"

"$10,000," Bing announced through his rich voice and looked among the other men who were bidding. Dean felt his knees go weak at the power in Bing's voice, daring someone to speak above him.

"Going Once! Twice! Sold! To Mr. Crosby for $10,000!"

Applauds filled the room and Dean looked around, unsure of what he was supposed to do now that he had been bought for the evening. His thoughts were interrupted when Bing's voice filled the room yet again, "Come here, boy! Right here!"

Dean walked over to him and stopped. He felt his back tensing as every eye in the room was on him.

"Good, lad. Now, take this key up to room number 218 and wait for me," he said and took Dean's hand, placing the key against his palm. He pulled the young crooner closer to him and whispered in his ear, "This will be a night _you'll_ never forget. Go ahead now."

Dean turned to walk to the stairs to go up to the room. Still in a bit of a shellshock, he wasn't so out of it as to get on one of the elevators.

Bob walked over to Bing and sat next to him and shook his head.

Bing rolled his eyes and said, "Don't look at me that way."

"When did you plan on doing this?"

"Somewhere around _The Road to Bali_ , Junior," he replied while watching Dean disappearing from sight. "And really…  Can you blame me?"

"Well… All I can say is don't wear yourself out, old man."

"Don't worry about me, my boy. I won't," he said and stood up, walking towards the elevators.

####

Dean found Room 218 and opened the door. He stood in the doorway, looking around the luxurious suite filled with fresh flowers. The warm tones put him a bit more ease and he stepped inside, shutting the door behind him.

He saw the bar at the far corner and took off in a stride to go mix himself a drink. Finding the Jack and Coke, he put a few ice cubes in and dipped his finger in the liquid. He touched it behind his ears and downed the drink in one gulp.

"Boy, oh boy, what have I gotten myself into?" he asked to no one in particular.

Taking out another cigarette from the case, he lit the end and tried to calm his nerves the best he could before Bing showed up in the room. He had never thought that this day would come and, now that it was here, he wanted it so badly on the one hand.

On the other hand, he wanted to run as fast as he could.

Mixing himself another drink and smoking his cigarette, he did entertain the thought that all the worrying he had was in vain. All he knew for sure was that he was going to be Bing's slave until tomorrow. Whether that meant the older man's sex slave or house slave was still relatively unknown.

"For that much cabbage, I guess he can do whatever he wants to do," Dean laughed as he talked to himself.

Just as Dean butted out his cigarette, the door opened and Bing walked in with such an air of confidence that it took the younger man's breath away.

The smoke was rising from the ash tray as Bing walked closer. The older man pointed to it and said, "Now, boy. I don't believe I gave you permission to sully my room with that stench."

"Well, I figured since you smoked that I could, too."

"And because I can sing, you think you can sing as well. Is that how this works?"

Dean's features softened as the remark took him a bit off guard and said, "Well, I do try."

"I see. And I also see that you helped yourself to my bar."

Dean looked down at the glass containing just the ice and looked up at Bing with a small shrug.

"Do you know what's expected tonight, boy?"

"I have a bit of an idea," Dean said with a smirk as he spread his arms out and placed his palms down on the top of the bar.

"Care to share with the entire class?"

"You asked me to do this charity auction of myself. You didn't tell me that there weren't any broads."

"You didn't ask."

"Didn't cross my mind to ask. I naturally assumed -"

"And, my dear boy, you know what they say about people that assume."

"Well, I guess you won me as your slave. The only question is, what kind of slave is it that you got in mind, paesan?" Dean asked, losing control of his accent. The uncertainties of everything was building up too fast over the past year between him and Jerry. Dean, at least, had to know where he and Bing stood.

"My boy, you are far too tense," Bing said as he walked closer and took a seat at the bar. Raising a finger, "Pour me a drink."

Dean nodded and took out a glass, "I'm listening."

"You remember last year when you came to that telethon Bob and I were doing?"

"I remember."

"That was the first time I really looked at you. Jerry was screaming for me to come out but no one tells me what to do. So, I didn't go to the stage."

"Right," Dean said and pushed the glass closer to Bing.

"Well, you didn't scream or order me around. You are his partner but you are different in more ways than one. You didn't expect anything from me and continued with the show.  I stood off stage and watched your every move."

Dean nodded, "Go ahead."

"I have been watching your shows a bit closer since and have made it a point to play with you on the golf course. Today, the auction was happening again and I simply wanted to invite you."

Dean clenched his jaw and softly said, "I've been watching you closely for a very long time, too."

"That is quite evident, my youthful Italian crooner."

Dean bowed his head but kept his gaze on Bing's bright blue eyes, staring into him. He arched his neck, "Well, I am yours for the evening. What do you want me to do?"

"Come out from behind that bar for one thing."

Dean moved from behind the bar and walked closer to Bing, stopping in front of him and cleared his throat. Bing stood up and looked up at Dean, noting how he was quite shorter than the younger man.

"First of all, I want to see exactly what I bought. Take off all of your clothes."

Closing his eyes for a moment, Dean moved to shrug off his jacket and place it on the bar behind him. Next, the shoes came off while he started to unbutton his shirt. Bing smiled as Dean seemed to shrink in height.

"So, you really do wear those lifts, huh?"

"I do, I do," Dean said with a smirk and continued undressing until he was standing in just his boxers and undershirt.

"I did say 'all of your clothes', boy."

Dean felt chill bumps popping up all over his skin and shivered. He folded them neatly on the chair and stood in all his glory in front of Bing who was still fully clothed in his black tuxedo. With a slight shiver, Dean started to feel remarkably vulnerable in his current position even though he was still just a little taller than Bing but not by too much.

Bing started to hum as he looked at Dean, "Very nice. Stand in the center of the room and put your hands behind your head."

Dean licked his lower lip and did as he was told. Bing came up behind him and inspected his body. Though he had a thin frame, the muscles in the Italian's body were well formed and taut. His ass cheeks looked firm and Bing wondered just how firm they were before he reached his hands forward, grasping them tightly.

Dean's breathing hitched as Bing massaged his backside and crooned in his ear. He kept his hands clasped firmly behind his head and moaned while closing his eyes.

"Anymore wondering about what I'll have you do tonight, boy?"

The only answer Dean could form was a soft, low groan. Oh, how he wanted this and he could already feel some of the tension leaving his body. He rose to his tiptoes when Bing gave his right cheek a sharp slap.

"I asked you a question. Do you still wonder what I'll have you do?"

Dean could feel the pleasure coursing through his veins, wanting more. He whimpered at that deep voice behind him and whispered out in the language he had spoken for so long with the accent he tried so hard to lose, "No. Fai come vuoi. Io sono tuo schiavo." 

Bing leaned forward, planting tiny kisses on Dean's right shoulder blade.  

"I'm sorry, Junior. I don't speak Italian. Translate." 

"I said," Dean started as he tried to catch his breath. The blood rushing through him and his manhood standing at full attention. "I said No. Do as you wish. I am your slave." 

Dean leaned back against Bing and arched his neck as he gently swayed his slender hips. Bing moved his hands, grasping him firmly and pressing his fingers into the Italian's soft skin. He breathed in, losing himself in the spicy Woodhue cologne and groaning. The bulge inside his trousers was becoming painful.

"Turn around, boy. Undress me. Show me how much you idolize me."

Dean didn't hesitate. He'd wanted this for so long and he needed it just as much. Turning around, he quickly and carefully began to remove Bing's clothes and putting them next to his own. The younger man's body driven by passion, he wasted no time and unbuttoned Bing's trousers. With a deep inhale, Dean fell to his knees. Dean's tongue danced across his lips and he moved forward, keeping his back straight and took all of Bing with one swift motion. The older man gripped the strong shoulders to hold himself up as his entire body shivered in ecstasy in response to Dean's sensual ministrations.

"Mmmm. Such a good Italian boy," Bing moaned, feeling Dean's talented tongue.

Bing's words of praise sent Dean flying as he cupped Bing's balls in one hand, bracing himself as he took Bing even further to the back of his throat. The tip of his idol's cock hit Dean's throat over and over. Pulling back a bit too fast, Bing had to make him stop or the night would be over before it really started.

Dean's eyes softened as he looked up at Bing towering over him. "I do somethin' wrong? I can do better."

"Oh, sweet kid. You're doing beautifully. Come on," Bing said and took Dean by the hand, leading him into the bedroom. He directed Dean to lay on his stomach across the bed and moved closer to his warm, strong body.

"You did say I could do anything, right?"

"Anything you want," the younger man purred.

Bing moved both hands over Dean's body. He let his left hand rest on the small of Dean's back and the right across both of his firm ass cheeks. Dean gripped the comforter between his fingers and closed his eyes. With him and Jerry, he'd always been the top but it only seemed natural to be like he was for Bing. Arching his back, he had expected Bing to prepare him and was shocked when a sound smack came across his bottom.

And then again.

And again.

Bing picked up the pace and was relentless in spanking Dean. The younger man spread his legs out a bit but didn't protest. It was different but felt surprisingly like heaven at the same time. Unsure if he would try to escape or not, Bing pressed down on Dean's back a bit more to hold him in place and was pleasantly surprised when Dean pushed his ass up to invite more swats instead of trying to evade them.

"Naughty boy. You like that, do you?"

The sweet sounds coming from Dean's throat sent Bing into overdrive. He stopped the spanking and took a moment to catch his breath. Leaning over to the nightstand's drawer, he took out the baby oil and moved between Dean's legs. Pouring the oil upon the olive skin before him, he gently massaged the man's  tense muscles and moved his fingers in between Dean's cheeks. Pushing his finger in, he worked the muscles to relax his slave for the evening.

"Just stay calm, Dino. Relax."

Dean rested his forehead on the large mattress and didn't notice when Bing took two pillows from above him. Bing put them under his hips, elevating him, and continued to work his tight orifice by introducing a second finger. Arching his neck to the side, Dean yelped in pleasure and didn't even try to contain his moans and whimpers. With each passing moment, more and more of the stress melted away from him. Dean tried with every fiber of his being to take the two fingers. Just as he became comfortable, Bing pushed his limits again when a third finger pushed inside him. Dean felt his body tremble as Bing hit his sweet spot.

Licking his lips, the new sensations were driving his mind into another place. He rose his chin for a moment and wondered how he didn't noticed before that there was a giant mirror in front of them. Feeling the fingers leaving him, he watched as Bing rose to his knees as started to line his manhood up to him. Gulping, he caught a glimpse of Bing's size and was a bit intimidated but he wanted this so bad. He pushed his legs a bit further apart, keeping his hips on the pillows, and arched his back a little more. Holding on to the comforter a bit tighter, he looked right into Bing's eyes through the mirror and those gorgeous azure eyes stared back into him.

Positioning himself and resting the head of his throbbing member against Dean, he grinned."You sure you're ready?"

"Ready as I'll ever be."

"Good boy," Bing said with a few more slaps to Dean's ass before he thrust into the willing body beneath him.

Pushing in and out, he worked slowly to give Dean a chance to accommodate his size. Bing was grateful that the place they were staying at was private. He was making Dean reach high notes louder than the man probably ever had in his entire life. Dean's eyes started to roll to the back of his head and he closed them, losing every bit of himself in the moment. Bing moved his hips faster and faster, gaining pace as he slammed into Dean.

The older man knew that he wouldn't be able to contain himself any longer and held on to Dean's hips tighter. Fingernails marking his skin with half crescent moons. Dean moved his hips across the pillows, the sensations sending him to the edge.

Bing suddenly pulled his entire length out of the man below him, resting there for a moment before he slammed back inside with unrelenting force. Dean's loud moans seemed to never end. With one more unexpected shove, Bing finally released and filled his slave.

Dean threw his head back and moved every way he possibly could as he tried to take it all. Slowing his movements, Bing rested his hand on Dean's warm backside and gently started swatting him again with love pats. Moving his hand down, he grasped Dean's throbbing cock in his hand and started to pump him. Dean got up to his hands and knees as Bing worked him, both men watching themselves in the mirror.

"Oh, God!!!!!" Dean cried out as he finally came on the pillows.

When the last of him was released, he collapsed across the bed on his stomach and struggled to catch his breath. Bing fell next to him and laid on his back. He turned his head to Dean and winked,

"Beautiful work, kid."

Dean lazily opened one eye to look at Bing and smirked. "You weren't too bad yourself, old man."

"Watch it, boy. Your ass is still mine for at least another eight hours and I do have a belt over there."

The mischief in Dean's eyes couldn't be hidden even if he tried.

#####

On the other side of the door, the three men lit their cigarettes after listening to what was happening inside.

"Tell you what, fellas. The kid's got some pipes on him," Bob said to Jack Benny and Phil Harris.

"I shoulda went ahead and bid some more on him," Phil said through his cigarette.

"I was hoping someone would. I almost _did_ win him," Jack dryly said.

"Such a cheapskate, Jack. You tellin' me that a night like Bing's having isn't worth that much? You heard the kid moaning, right?" Phil asked.

"It wouldn't have mattered what you two dopes would have bid. Dad wanted Dino and he got him," Bob laughed.

"Come to think of it. You didn't bid a cent, Bob," Jack said and tapped some ashes off of his cigarette.

"Didn't have to. I'll get my chance. Don't you worry," Bob said with a mischievous grin and butted his cigarette out in the hall ashtray.

Jack and Phil watched Bob waltz off to his room humming _That's Amore_.

~      

 

 

 


	2. The Morning After

**Summary for the Chapter:**

> Dean wakes up in the middle of the night and decides to sneak back to his room. The next morning, Bing isn't too thrilled about his decision.

Dean arched his neck and nestled into the pillow under him as he slept on his stomach. He quirked an eyebrow when he heard the person next to him snoring softly. Chewing on his lower lip, he squinted his eyes and looked at the clock showing 2:30 in the morning. Gripping his soft pillow, he looked next to him and saw Bing sleeping as sound as a baby.

The younger man's mind was filled with the memories of what happened just a few hours prior and swallowed hard. As he started to recall what happened, he clenched his bottom and the gentle reminder was definitely still there.

He figured that Bing was through with him for the night and would let himself out. 

Slowly, he started to slide out from under the sheets and felt the cool breeze cover his naked body. He didn't want to disturb the older crooner's sleep and moved silently towards his pants, deciding to slip them on and just gather the rest of his clothes in his arms. Tiptoeing towards the door, he opened it slowly and snuck out as he closed it shut just as quietly. Leaning his back against the wall, he gulped and wiggled his bared toes against the soft, blue carpet.

"What a night," he whispered to himself as he made his way towards the stairs to go to the third floor to his room.

####

Bob grabbed the morning paper from the floor and nestled it under his bicep. Humming to himself, he opened his door to make his way to his partner's room. He wondered if he would be able to walk in on him and Dean.

Walking down the hallway, he reached in his pocket to grab the key that Bing gave him when they'd first arrived and pushed it into the lock, opening the door, and saw Bing sipping on a cup of coffee as he sat at the breakfast table.

Shutting the door, he walked over towards Bing and dropped the morning paper on the table.

"Sleep good, old man?"

"Don't start with me, Junior. I've not even finished my first coffee."

Bob winced and lowered himself in the chair across from his friend. Crossing his leg, he reached in his pocket to retrieve his cigarette case. He tapped the filter against the metal before he lit it. He looked the room over and narrowed his eyes, "Hey? Where's the goombah?"

Bing sighed and reached for the paper. He swallowed down the last sip of his coffee and said, "I said that I don't want to talk about it."

Normally, Bob would press the issue but he also noticed that Bing wasn't even smoking his pipe like he normally would so he thought better of it. They sat in silence for a few moments and both turned their heads when they heard a short knock followed by Phil Harris walking through the door.

"Well, well. Good morning, fellas!" Phil said with a friendly grin as he waltzed over towards the table and took his seat. "What's happenin'?" He asked as he leaned over and grabbed the coffee to pour himself a cup.

Bing looked at Phil and pressed his lips together. He raised the newspaper to cover his face and said in an even voice, "Morning, Harris."

Phil looked over at Bob and swallowed. He mouthed to the other man, "What's going on?"

Bob shrugged while he shook his head and took a cigarette out of his pack, offering it to Phil.

"Where's Dino?" Phil asked as he lit his cigarette. He knew it didn't take much to annoy Bing and, if he was, it'd be even harder to make amends with the crooner - if ever.

He was curious as to how angry Bing was and he got his answer when Bing answered in a smooth voice, "How should I know? I only paid for him for a night. Not the rest of our lives."

Bob and Phil shared a quick glance.

Both of their faces read the same expression - "Oh, shit."

"Look. You fellas enjoy your breakfast. I'm going to get an early start on our last day here and go on to the course," Bing announced as he got up and put the paper down. He grabbed his hat and licked his lips before finishing off his second coffee. "I'll see you both out there."

Bob and Phil didn't have a chance to say anything as Bing walked towards the door. Phil looked over to Bob and shook his head.

"Man, oh man. I wonder what happened after we left the hall last night," Phil said as he reached over to grab the knife to spread some butter on his toast.

"Beats me. You seen Dean this morning?" Bob questioned while he put his cigarette out in the ash tray. 

"I didn't see him but I heard him in his room earlier this morning. His is next to mine and I think I heard the shower going."

"Uh huh. That explains it."

"Explains what?"

"Looks like the kid decided to skip out on Dad early this morning. You and I both know how he hates being left like that."

"You and I do but how's the kid supposed to know?"

"Either way, Bing is a bit miffed and it'd be wise if Dean made himself scarce until this gets sorted out," Bob said and stood up, walking towards the door to make his way up to the Italians's room upstairs. 

####

**Notes for the Chapter:**

> Felt the urge to continue this story and this idea came in my mind. Will be posting the next Chapter soon but not sure how many chapters this story is going to have.  
> If you like it, would you be so kind to leave me a comment/kudos/feedback? They do keep the muse talking to me. :) 
> 
> Thanks so much for reading!


	3. A Very Good Talking To

**Summary for the Chapter:**

> Bob takes it upon himself to explain to Dean where he went wrong...

Bob stood tall with his hands behind his back as the elevator made its way up to the third floor. He narrowed his eyes for a moment and pressed his lips together in a thin line while thinking about how to approach Dean with what was going on.

The kid was talented, handsome, and had a hell of a sense of humor. Unfortunately, he had also noticed that sometimes he had a knack for doing something not _that_ smart. To be fair, he didn't know Bing like he did and he wanted to give Dean the benefit of the doubt.

He snapped out of his thoughts when he heard the chime that the doors were opening and stepped outside, turning right to make his way to Dean's room. Looking at the numbers, Bob finally found Room 323 and rose his hand to knock on the door.

As luck would have it, the door opened as his knuckles rapped on Deans's forehead.

"OUCH! Hey, what gives?" Dean stood back and held his forehead.

"Glad to see your head isn't made completely out of wood, blockhead," Bob said and pushed his way into the room. He couldn't help but notice the suitcases were packed. "Hey, you cuttin' out already? We got another night here, you know."

"Well, I wanted to get back to Palm Springs. And whaddya mean 'blockhead'?

Bob shook his head and walked over to the couch, plopping down, and crossed his legs. Dean clenched his jaw and rubbed his hands together, "Not to be rude but did you miss the bit where I said I was leaving in a little while?"

"I don't think you should but, of course, it's not up to me and it's totally your business if you want Dad to go around angry at you."

"Huh? What did I do? I did my… my… slave bit last night for him. I did what he asked."

"Uh huh. I know. Matter a fact, most of the second floor heard. But let me ask you this, paesan," Bob said as he got up and stood in front of Dean. He reached forward and straightened the dark red sweater the younger man was wearing and stood nose to nose with him. "Did you happen to leave in the middle of the night?"

"I woke up earlier and he was asleep. I just let myself out and didn't think nothin' of it."

"And that's your problem, meatball. You didn't think."

Dean swallowed, "Now why is he upset over something silly like that?

"He doesn't think it's silly at all. I'd suggest staying for another night and making it up to him."

Dean sighed and reached in his pocket to retrieve his cigarette case. He stepped away from Bob and went to his bar, "This is crazy, Bob. It's not like I'm his girlfriend for Christ's sake!"

"Look, Dean. We all have our different quirks. I'm sure there's things that you know about Jerry - what ticks him off - that other people don't. And I'm sure there's things about yourself. When we come here for the weekend, Bing expects to have a good time and to be treated with respect. You didn't realize it, I get that, but now you know. So, the question is, you loud little minx: What are you gonna do about it?"

Dean took a drag off his cigarette and smoothed out his black trousers, wiggling his foot on the barstool. "Really? I have no clue how this all works. I've only ever fooled around with one other man in my life and I was always the top. And, to be frank, I never gave a shit what Jerry did after we were done."

"Oh, kid. You're hardheaded as hell and gonna make me lose what hair I got left. What it all boils down to, now pay attention, is Dad felt jilted. He spent ten thousand clams on you last night and you left way early."

Dean nodded and took another long drag, raising his pointer finger up to his lips and started tapping them. He sighed and nodded, "Alright, alright. So, what do I do?"

Bob walked closer to him and leaned on the bar, smiling at Dean. The older man reached his hand out to caress Dean's right cheek.

"Well, from what I heard last night, kid. I'm sure you can think of a thousand different ways." He couldn't help but chuckle when Dean started to blush.

Dean swatted Bob's hand away,"Cut that out. Were you out there listening or something?"

Bob shrugged and grinned impishly, "Maybe I was. Maybe I wasn't."

Dean butted out his cigarette and went over to the phone to cancel his leave and tell them he'd be staying another night. Bob leaned with his back against the bar, resting both elbows, and kept his eyes on the younger man. The way he rested the base of the phone against his hip, his bottom slightly jutted out, and the subtle arch of his neck was driving him crazy. Especially when Dean straightened his back just a bit and he could see the way his trousers fit tightly around his firm backside.

Licking his lips and clearing his throat, he watched as Dean hung up the phone and Bob walked closer to Dean. He reached to give the younger man a firm squeeze and laughed when the Italian rose to his tiptoes. Slapping Dean's bottom squarely across both cheeks, "I'm sure you'll have no problems making it up to Bing."

Dean swallowed hard, "It seems you both have something in common - a strange fascination with my tutu."

Bob leaned forward and whispered in his ear, "You have no idea. Also, forgive me but even I can't resist the temptation."

He turned Dean around and pulled him closer. Bob leaned inand kissed him softly on the lips, moving his hands down to get a solid grip on his pockets, bringing him in closer. He pushed his manhood against Dean, groaning, and held the younger man in his arms and smirked as he felt the Italian squirming and moaning in response. He pushed his tongue into Dean's warm mouth, tilting his head and tasting the cigarette he had just finished smoking mixed with the minty toothpaste. Closing his eyes, Bob felt his nostrils flaring and found himself lost in Dean's scent and taste.

Dean's knees buckled and he closed his eyes, moving his hands around the small of Bob's back to hold on and hoping he wouldn't fall backwards. He had no need to worry as Bob held on to him even tighter, moving one free hand down to cup the Italian's right bottom cheek and squeezed hard.

Slowly opening his eyes, Bob broke the kiss and leaned back, lightly tapping Dean's bottom. Dean swayed his hips against Bob and shivered. Keeping his eyes closed, Dean heard Bob's voice saying, "You know, you really are a good boy. Maybe after you and Dad patch things up, you can come over to my room later and thank me."

Dean closed his eyes and cleared his throat, "What... What are you gonna do to me?"

Bob leaned forward, grazing his lips against Dean's ear, and whispered, "You just bring yourself. I'll worry about the rest, kid."

"Between you and Bing, you both are gonna wear my ass out."

Bob looked down and grinned, his eyes going from the raised tent in the front of Dean's trousers and his own. He looked up to meet Dean's liquid brown eyes, "You can bet your sweet bippy on that."

Bob grabbed Dean's shoulder, spinning him around close to the bar and directed him to lean over.

"A little preview of what you got coming to you, boy."

Dean placed both hands on the cool, hard wood and felt Bob's foot kicking his legs apart while keeping a hand on the small of his back. Bob pushed against the younger man's back gently, causing him to arch and jut his bottom out, and let his other hand rest across the black trouser clad bottom.

"Wayward boy. Tsk tsk. What should I do with you?" Bob asked as he eyed the thin fabric leaving Dean with hardly any protection. 

Dean licked his lower lip and kept his head bowed, having a feeling where this was leading. His instincts were right when he suddenly felt sharp smacks raining down on his ass. Groaning and moving his hips from side to side, he held on to the bar as Bob spanked him over and over again on his already sore bottom from the previous night. He threw his head back, feeling himself growing even harder. 

"Now, now, boy. Don't be afraid of vocalizing for me. You've got such a sweet, sweet voice," Bob said with a grin as he spanked the Italian harder. "Or do I have to take down these pants?"

Dean was surprised by the amount of power Bob had in his swings and grunted. He gripped the bar harder and bent his knees. Lowering his head, he couldn't hold back any longer.

"Ouch!!! AHHHHH!"

"See? That's much better," Bob said and gently patted Dean's backside. The older man reached his hand around, feeling the outline of Dean's cock and rubbed his hand over the hardness. Moving his hand down lower, he grasped Dean's balls and squeezed gently. "We'll have to finish this up later, goombah. And that's a promise," he said before he let go of Dean. 

Dean looked over his shoulder, still holding on to the bar for dear life, and swallowed hard as Bob let himself out.

"Meet me in my room - 228 - when you and Dad are finished."

Being left in his current state and his intense hard on, he started to get the idea of why Bing was so cross about him leaving like he did last night and whimpered.

"Damn."

####

Bob walked back towards the elevator with a sly grin on his face, jingling the change in his pocket. Tapping his foot, he waited for the elevator to open and smiled when he saw Phil getting off the elevator.

"Did you talk to the kid, Bob?"

"Oh, I gave him a very good talking to," Bob said with a wink.

Phil shook his head and laughed as he continued on to his room.

"I'll see you on the course in a bit, Bob."

~TBC

 

**Notes for the Chapter:**

> I own nothing of the estates of Bob Hope, Dean Martin, Bing Crosby, or Jack Benny. This is entirely written for entertainment and no profit is ever made from these fanfictions.


	4. Friendly Advice

**Summary for the Chapter:**

> Phil Harris comes by to offer some friendly advice which motivates Dean to take action to seek out Bing to apologize. Only question is, will Bing be in a forgiving mood?

Dean held himself up at the bar with both hands and tried to calm his labored breathing. He felt his eyes glaze over and his rock hard cock throbbing after being left in agony by Bob. When the door shut after the older man left, Dean quickly unbuttoned his pants and reached for his throbbing member, groaning and moaning as he bit his lower lip.

"Damn him for leaving me like this. Fuck," Dean said through gritted teeth and threw his head back as he came. Body spent, he leaned over the bar and tried to catch his breath.

Just as he reached to grab a towel to clean himself off, he heard a soft knock at the door.

Licking his lips and trying to calm his voice he said, "Who's there?"

"Oh, Mr. Martin. You in there?"

"Yeah. That you, Mr. Harris?"

"It is, it is. You decent? Can I come in?"

"Gimme a second," the younger man said and hurried to compose himself. He mumbled to himself about how indecent he was and tried to hurry up but still couldn't wrap his head around what he had gotten himself in for with this trip. His intention for even coming here was for it to be a relaxing golfing vacation with his pallies. He walked over to the sink and quickly washed his hands as well as ran a comb through his hair.

Breathing out heavily, he walked gingerly to the door and saw Phil standing there with a huge grin on his face.

Dean narrowed his eyes and nodded, "What you grinnin' at?"

"Oh, just happy to be here. Can I come in?"

"Sure. Why not?" Dean said and stood to the side to let him in. 

'How'd last night go?" Phil asked as he strolled over to the couch and took a seat, patting the seat beside him.

Dean walked over to him and sat down carefully; wincing as he lowered himself and tried to cross his right leg over the left.

"Well, I thought it went good. Think I made Bing mad, though."

Phil tried to stop himself from laughing at Dean's discomfort in trying to do something as simple as sit down. "Oh, I don't think you made him mad, Dino."

"You don't?" 

"Nope. I _know_ you did," Phil said and laughed. The older man leaned forward to grab Dean's cigarette case and smiled, "You mind?"

Dean shook his head and felt his heart drop, "Go ahead. I was afraid of that seein' as Bob said the same. Guess I really have a lot to make up for…"

"It ain't gonna be easy, pal. I'll tell you that. Bing doesn't forgive and forget so easy. He's a good fella, sure. But he's tough."

Dean bit his lower lip and nodded. He whispered, "I really didn't mean nothin' by leavin' like I did last night. Jerry does, or did, me that way and I never care. I don't know what to do to make it right."

Phil nodded and took a drag off his cigarette. He watched as Dean fumbled to light one of his own and put a hand on Dean's shoulder. "Look, kid. I know you didn't mean anything but Bing is just like that. Just because he's tough, doesn't mean you can't try. Who knows? You may be the exception to that rule of his."

"You think so?"

"It's worth a shot and it couldn't hurt. He left just a bit ago to get ready to play the golf course. He's probably trying to simmer down from the way I see it. He didn't even have his typical pipe this morning. Usually, he carries on no matter what - business as usual. You must have really thrown him off."

Dean nodded and crossed his arms while slowly dragging on his cigarette. He tilted his head thoughtfully and smiled a little, "What would you do if you were me?"

"Well, I have been up for auction before - long ago and a slave for the night. This your first time, right?"

"That's right. Never been a bottom or even spanked like Bing and Bob have done me."

"Bob spanked you, too?"

"Yeah. Just a bit ago."

"I'll be damned. I can't blame him, though. I'd love to give you a warm up. You do have one hell of a cute backside, baby."

Dean arched a brow and chuckled, "I'm already pretty warmed up but thanks. I think..."

Phil leaned back and got comfortable. He butted out his cigarette and said, "Look, kid. I like you or else I wouldn't be here. You can do what you want but I will say this as my advice. Just go to Bing and be honest. Apologize to him. I've been on both sides as a bottom and a top, though, I am more of a top nowadays. Bing has always been a top."

"Yeah. I was like that with Jerry for the last few years."

"Think of how you'd like Jerry to apologize for something he did, then. Work off that."

Dean furrowed his brow and swallowed hard. If he were to be truthful with himself, he had thought of that a lot lately. He hated the feud he had at the present with Jerry and how jealous he got when his song hit number one. That night he went overboard and pulled his hair, smacking him around, was not a night he enjoyed. He was trying so hard to keep his cool but he'd absolutely love it if Jerry would just apologize and do it sincerely.

Dean heard Phil snapping his fingers, "Hey? Oh, Mr. Martin? You still with me?"

Dean broke out of his thoughts and nodded, "Yeah. Sorry. I think I get what you're saying. I'll make good with Bing."

Phil slapped Dean's knee and smiled, "That's what I like to hear. You'll be just fine, baby. But put out that cigarette. You're about to burn your fingers off."

"Shit," Dean said and quickly put the burned up cigarette in the ashtray.

Phil smiled, giving Dean a kiss on the cheek, and stood up, "I'm going to meet Bob but you can come by my room later if you want when I get back. I'm just across the hall from you. Speaking as your pal, I wanted to make sure you're okay. As far as Bing is concerned, he loves it when his boys kneel before him but do it sincerely. He can tell  if you're just joshin' him and I think you really are sorry about it all, so you'll be fine."

Dean stood up and walked Phil to the door to let him out.

"I really do appreciate you coming over here."

"No sweat. I'll see you tonight at dinner," Phil said and let himself out.

Dean looked up at the ceiling and swallowed. He had a lot of work to do.

#####

Dean walked into the gentleman's room and breathed in the freshly clean scent of the space. He stood at the door and took his surroundings in and watched as the waiters pushed trolleys filled with liquor and snacks.

Though there were men sitting at different tables and lounging, the conversations were soft. The mahogany room felt relaxing yet a strong no-nonsense vibe was definitely felt. He saw Bing far across the room, engrossed in a book he was reading. Dean licked his lips and reached out to grab a glass from the cart to wet his whistle.

"Would you like anything else from the trolley, Sir?"

Dean shook his head, "Thanks but not right now, fella."

Dean drank the cool water down in one gulp and gave the glass back to the waiter before he started to stroll across the room. He was careful to keep his chin high and back straight. Though he was nervous, he'd learned over the years to always walk with confidence no matter what. He made his way to Bing and stopped in front of him, clearing his throat. Bing look over the book he was reading. Dean looked down and smiled at the older man, noticing it was a book about race horses.

"Got any good tips?" Dean smiled.

Bing arched an eyebrow and closed his book. He stood up and put the book under his arm, clearing his throat and said softly, "I have but one tip for you, Mr. Martin. Don't make a bet that your ass can't pay."

Dean opened his mouth to attempt a reply but Bing had already walked away. The younger man felt his cheeks burning and the back of his throat feeling bitter. He lowered his chin and closed his eyes in defeat as he whispered, " _Oh ragazzo_."

Far across the room, Bob and Phil watched the pair and looked at each other with concern as Bing walked away, leaving the younger man standing alone. 

Phil grimaced and Bob nodded, "Not so good."

"You ain't whistlin' dixie there." 

"Not bad, either, though."

"Whaddya mean?"

"Dad did say something to him. If he's truly pissed, he'll completely ignore you, ya know?"

Phil nodded and said, "That's true. There's still some wiggle room here. I'll help out the kid and you got Bing?"

"That's the ticket," Bob snapped his fingers. 

"Let's get to it."

####

TBC

 

**Notes for the Chapter:**

> I am so sorry it's taken awhile to post this story and continue, my pallies! 
> 
> Loads of things going on but I am not going to abandon this story. Thanks so much for all of the kudos and the comments. I do love them and appreciate it so much. 
> 
> Also, if any of you have any ideas on how to progress the story, feel free to let me know and I'll see how I can work that in to the conclusion. 
> 
> Again, thanks for your patience and hope you like this new chapter. Will be back soon and won't be away nearly as long. :) 
> 
> Btw, Oh ragazzo means "Oh boy."


	5. I Am What I am

**Summary for the Chapter:**

> Dean decides it's time to leave but Phil and Bob think he should stay a bit longer. Can they convince him to stay and will Bing come around?

Bob looked at Phil and bit his lower lip, "Now listen. You go on and talk to Dean, alright? I'll catch up with Dad and see if I can't smooth over this whole thing and get him to listen."

Phil turned around and looked at Bob, taking a cigarette out of his case and fumbled for a lighter. He leaned forward when Bob struck a match for him and took in a long drag. Phil took the cigarette out of his mouth and he said, "Got any advice on what I should say to Dean?"

"Just make sure the goombah is alright. I know him but I don't know him well enough how he's taking all this. He's something of an enigma."

"He really is," Phil said as he turned around to where Dean was and didn't see him. He gazed around the room and didn't see him at all and arched a brow, "Where'd he go?"

"Wherever he went, he sure moves fast."

Phil nodded, "Go on to Bing. I'll find Dino." Harris took a drag off the cigarette and strolled off to find Dean as Bob left him to go to Bing.

****

Bob walked out of the lounge room and had a pretty good idea where Bing  went. He went to the locker room, figuring that golf was definitely Dad's home away from home and helped him clear his mind. The good news was is that Bing _was_ trying to clear his mind which meant, to Bob, that he had already forgiven Dean. Normally, he'd just go to his room and distance himself from anyone but he hadn't this time. Not to mention he actually spoke a few syllables to the young Italian.

Bob walked into the locker room and up to the slightly older man as he was getting dressed as well as his clubs ready for a game.

Bob leaned against the lockers and narrowed his eyes a bit, "Fancy seeing you here."

"I'm not in the mood, Junior. What are you doin' here?"

"Oh, just about to sell some souvenirs."

Bing couldn't help but crack a smile and said, "If you're trying to calm me down about Dino, you may as well not waste your time. We've only got one day left here, after all."

Bob pushed himself off the lockers and walked closer to the other man. Bing grabbed the rest of his belongings and headed out the door so he could go play a few holes but Bob wasn't letting him get away that easy.

"Now, you just wait a minute, old man. You know Dean but you don't _know_ him. I get that what he did rubbed you the wrong way in leaving but didn't he …well, rub you the right way before that?"

Bing narrowed his eyes and turned around, "Junior…"

"I have been your partner for a long time now. I've been in Dino's shoes with you and all I'm sayin' is, the kid didn't mean a thing by it."

"I paid good money for that boy last night and he just left…"

"After he did what he thought you wanted. Look at it from his side of the story. Did you tell him to stay all night?"

"Well, not in so many words but he should have known. That was a complete lack of respect for…"

"Dad? Really? You're not exactly the most vocal about your needs and you can't assume that people know what you want."

"Junior, I do appreciate you trying to smooth this over with Dino and myself. I merely want to play a game of golf and then relax for the rest of the day before I retire to bed. The boy made a mistake last night and I would rather not see him or talk to him right now. Now, if you will excuse me…"

Bob's nostrils flared and he smoothed out his jacket, throwing the cigarette butt on the floor and walked in front of Bing. "You listen here, pal. That boy has a heart of gold and puts up with a lot of shit. You and I both know it and, in case you forgot, he does respect you. Remember that telethon and how he backed off when Jerry was badgering you? If you want to be angry at him for the rest of your life, go ahead. This entire thing is ridiculous…"

"You have a point but, really, it's not any of your concern. Again, if you'll excuse me…"Bing said as he walked out of the locker room and to the golf course, feeling his cheeks on fire.

Bob's jaw dropped open and, though he'd known Bing for years, still could hardly get over how stubborn that man was. Shaking his head, he left the locker room and headed back to the hotel. Not exactly feeling like walking all across the huge grounds, he hopped into a golf cart and head back - trying to wrap his head around what happened.

When Bing stepped into the sunshine, he handed his bag to the caddy, hardly able to wait to play a game by himself. As he walked across the green, he clenched his jaw and made his way to the first hole to tee off. He took a deep breath in and considered  that he maybe Bob was right.

He did like Dean - a lot - and had respect for the younger man. Dean was charming, well spoken, and humble.  He furrowed his brow for a moment as he realized something even more important. He had been Dean's first and he stopped mid-swing as this fact dawned on him.

He lowered the club to the ground and looked up to the sun, realizing how much Bob was right. He knew Dean on the surface but he didn't really know him well enough. Taking a deep breath, he decided to pack his golf clubs and try to find the Italian crooner.

****

Dean put his hands in his pockets and started to exit the lounge.

He knew that Bob and Phil wanted him to make amends with Bing but he couldn't make the older man forgive this misunderstanding. As far as Dino was concerned, he gave it a shot but Bing didn't want to listen or even try. He gazed over at Bob and Phil talking, figuring it was about what just happened, and darted out quickly before they could confront him about the decision he was about to make.

The entire point of this trip was to relax for awhile away from Jerry to collect his thoughts. He didn't want, or need, or need this aggravation and was determined to head back home for the long drive.

Dean took a deep breath and clenched his fists in his pockets as he made his way up the stairs to his room to finish packing his things and call the bellboy to help him to his car. He rubbed his sore backside, making a sour face. Sometimes, it was better to just get some time alone to collect your thoughts.

He smiled a bit to himself and was thankful he didn't unpack earlier when he canceled the first time.

He wanted out of there and to get some time to collect his thoughts.

He loved Bing's singing and his style but he didn't want to take flack from the older man and had no intention of doing something he didn't want to do. It wasn't in his blood to take too much from someone and wasn't going to bend if he didn't feel right about it.

He would call Jerry, Frank, and anyone else out - including Bing.

Sure, he enjoyed their romp between the sheets last night and the way Bing played the drums on his tutu. Both were new and pleasurable sensations but he wasn't going to beg someone who wasn't even going to listen to his side of the story.

He shook himself out of his thoughts and went to the door when the bellboy came to his room knocking to help him load up his bag.

 "Thanks, Pallie. Help me get outta here quick and I'll give you a good tip."

The bellboy smiled and got to work on loading up the Italian's golf bags, luggage, and shopping bags. He worked rather efficiently as Dean had asked and  Dean handed him a hundred dollar bill.

 The boy took the tip  with a smile, "That's everything, Sir. Are you ready to get on the elevator?"

"You take the elevator. I'll take the stairs and meet you downstairs in the lobby."

"Whatever you say, Sir."

The two made their way down to the lobby and out to Dean's car to load up vehicle with his luggage and clubs. Dean ran his fingers through his hair as he sat behind the driver's seat and put on his sunglasses while the bellboy closed the trunk.

"Thanks, Pal," Dean said as he started the engine and lit a cigarette.

Bob looked over, squinting his eyes, as he pulled up to the hotel in the golf cart and saw Dean about to take off. He floored the cart and rushed past Dean, stopping the cart in front of Dean's car.

Dean looked up at the sky and rose both hands up in the air and his thick accent came through as he said, "What are ya doin' to me, Paesan?"

Bob hopped out of the cart and walked over to Dean's car, putting both hands on the door and leaned down.

"Where you think you're going, goombah?"

"Look. I really appreciate all your doin'. Bing ain't gonna listen and I don't want to waste my time. Now, if you'll just move along…"

"Not happening."

Dean groaned and took off his sunglasses, "I already checked out and I'm heading home. Now, Mr. Hope, if you please."

"Meet me up in my room for lunch. If you still want to go after that, be my guest. Deal?"

Dean clenched his jaw and did realize he hadn't even eaten yet this morning. He looked deep into the older man's eyes, causing Bob's heart to skip a beat when he stared back into Dean's liquid brown ones.

Dean chewed his lower lip, "Make it a Pastrami and it's a deal. And no tricks."

"What do I look like? A magician? C'mon, kid."

Dean turned off the engine and got out of the car, throwing the keys to the bellhop.

"Park it for me and I'll be back in a bit. Take good care of her," Dean said and stood beside Bob.

As they walked back up to the hotel and made their track to Bob's room, Phil came over to them. "Hey, baby. Where'd ya go? You're quick."

"You ain't foolin'. I just caught him trying to escape."

Dean tilted his head, "I ain't escapin nobody. I just wanted to get home."

"Oh, now, Mr. Martin. Why would you want to leave so soon?" Phil asked and threw an arm over Dean's shoulders.

Dean shrugged his shoulders and looked at the two men as they walked towards the elevator, "I don't know. Just wanted some peace and quiet. I'm not getting on that elevator, though. I'll meet you guys upstairs. Room 228, right?"

"Right," Bob said and went to get on the elevator with Phil. "Meet you upstairs."

Dean looked around as he watched them head towards the elevator smirked a bit to himself.

He made his way towards the stairs and looked up at the ceiling, shaking his head. Part of him wanted to go with them and the other part said to get the hell out of there.

"Fuck it," he muttered to himself and turned heel, making his way back outside to his car. Phil walked up behind him and put a hand on his shoulder.

"Now, baby. Don't ya be tryin' to leave me," Phil said with a chuckle leaned down to pick Dean up and hoisted the younger man over his shoulder, heading towards the stairs to take him up to Bob's room. Dean wiggled over Phil's shoulder as the older man walked him towards the staircase and they got halfway up while Phil held on to him by the small of his back.

Dean couldn't help but smirk a little bit and allowed himself to be manhandled by Mr. Harris. Truth be told, he knew he could break free if he wanted to but he couldn't help but be a little curious what these two were going to do with him.

 Bob walked behind them and took the stairs in case Phil needed help.

"Quit your squirming, boy," Phil said.

"Better listen to him, goombah," Bob chimed in with a smirk.

Dean was glad that they couldn't see the smirk on his face and he tried to sound as annoyed as possible when he shrieked out, "Put me down! This ain't right, old man. That goes for you, too!" He directed at Bob.

Phil stopped and raised a hand, "What did you just call me? Old man?" Phil said while smacking Dean square across both cheeks. "Now, sweetheart. Are you gonna calm down or am I gonna have to spank you?"

Dean winced and stopped for a moment, feeling  his face turning a blush red. Phil went to walk on but Bob stood in front of him and held up a hand, "Wait a minute. Did you just call me an old man, too, kid?"

"I…I…" Dean started but was interrupted by Bob's hand slapping both of his bottom cheeks rapid fire, causing him to shriek out, "OW!" Bob smiled at the sweet sounds coming from Dean and let his hand rest on the younger man's bottom, giving it a firm squeeze for both cheeks and tapping it gently.

Bob breathed in and smiled, "You've got one nice bottom for thrashing, Dino." Dean squirmed over Phil's shoulder and felt his manhood coming to life at the touch and words these two bestowed upon him. He lowered his head and groaned softly.

 They chuckled and continued to make their way to the top of the stairs and Bob opened the door for Phil, "After you!"

"You're too kind, baby," Phil said with a wink and continued to track to Bob's room while keeping his hand on Dean's trouser clad bottom. Dean swallowed hard and closed his eyes, losing himself in that intoxicating feeling. He stilled his body as Phil rubbed his backside gently and gulped, feeling more calm than he had all day.

Finally, the three men made it to the hotel room and Phil took Dean over to the table and Bob shut the door behind them.

"Alright, fellas. Take a seat and let's figure out what we want for our grub so I can call room service," Bob said and sat down as the other two men joined him.

Dean gently sat down and took a cigarette from his cigarette case and nodded, "Just a pastrami on rye for me will be fine. And, of course, to know exactly why you two don't want me to leave."

Phil and Bob looked at each other and then at Dean. Bob spoke up and nodded, "Fair enough question and we'll have the same. I'll make the order and we'll talk."

Dean sat back in his chair and rubbed the bridge of his nose, playing with the pinky ring on his left finger. Frank gave that to him not too long ago and he loved the emerald cut diamond. Of all the people in the world, Frank knew him probably the best and he kind of wished he was here to help him make sense of all this.

He chewed his lower lip and smoked his cigarette while Bob made the order. He peeked over at Phil and smiled a bit.

"I tried to catch up with you after what happened between you and Bing in the lounge, Dino. Where'd you go so fast?"

"Oh, I just wanted to get back home to Jeanne. Get some peace and quiet."

"But didn't you want to smooth things over with Bing?"

"Course I did. I went to him and he walked away. I ain't gonna chase after somebody that don't wanna listen though. Not my style."

"Thought he was an idol of yours, kid."

"He is and I have adored him for years but it is what it is. If he's mad and don't wanna talk to me after I tried, whaddya expect me to do? Way I see it, the ball's in his court now."

"Huh. You are quite an enigma."

Dean shrugged and looked at Phil, "I am what I am. When Bing's ready to listen, I'll talk but I ain't chasin' him down if all he's gonna do is walk away from me." The young Italian butted out his cigarette and got up to head over to the bar to fix himself a martini.

Bob had been listening to them as he put in his order with the hotel for room service and arched a brow. The more he found out about the Italian, the less he understood. He adored Bing but wasn't going to bend over backwards and beg the man to forgive him. He also thought of the scene that just took place in the stairs and how much of a submissive Dean could be at the same time. He was like a beautiful paradox. Strong but willing to submit if the conditions were right and he knew that Dean could have left if he'd really wanted to. He finished placing the order and hung up the phone, turning around to walk to the bar and heard a knock at the door as he was about to ask Dean to explain a bit more so he could understand.

Groaning at the interruption, he walked and answered the door to see Bing standing there.

"Junior. Is Dean here?"

Dean saw Bing standing at the door and slowly put his glass down on the bar. He whispered to himself, "Well, this could get interesting…"

~To Be Continued

 

 

 

**Author's Note:**

> I got the inspiration to write this particular story from a few different places. 
> 
> One was when I found Mrs_Don_Draper's works and reading all of her stories surrounding that era. They're awesome and you should check them out here: http://archiveofourown.org/users/Mrs_Don_Draper/pseuds/Mrs_Don_Draper
> 
> Secondly: After watching old Martin and Lewis shows (specifically the one where they show up on Bob&Bing's telethon). 
> 
> Third: This picture of Dean begging Bing in a game of golf here: http://www.stevenlewis.info/crosby/Martin&BingGolf.jpg
> 
> Fourth: I was trying to sleep and the muse was giving me the Slave Auction idea and wouldn't shut up. So, naturally, I had to write it. 
> 
> \---------------
> 
> Also, if you guys dig this and want me to continue ...just let me know. If this storyline peeks your interest, I'll talk to my muse and see what we can come up with. Thanks so much!


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